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Information on EC 5.4.99.47 - parkeol synthase for references in articles please use BRENDA:EC5.4.99.47
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EC Tree
IUBMB Comments The enzyme from rice (Oryza sativa) produces parkeol as a single product .
The enzyme appears in viruses and cellular organisms
Synonyms
2,3-Oxidosqualene cyclase, AK066327, CAS1Ile481Val, cycloartenol synthase 1 mutant I481V, cycloartenol synthase mutant H477N, cycloartenol synthase mutant H477Q, ERG7, ERG7H234Y, lanosterol-synthase mutant T384Y, lanosterol-synthase mutant T384Y/V454I,
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2,3-Oxidosqualene cyclase
cycloartenol synthase 1 mutant I481V
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cf. EC 5.4.99.8
cycloartenol synthase mutant H477N
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cf. EC 5.4.99.8
cycloartenol synthase mutant H477Q
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cf. EC 5.4.99.8
lanosterol-synthase mutant T384Y
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cf. EC 5.4.99.7
lanosterol-synthase mutant T384Y/V454I
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cf. EC 5.4.99.7
lanosterol-synthase mutant T384Y/V454L
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cf. EC 5.4.99.7
OSPC
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oxidosqualene:protostadienol cyclase mutant in which the residues 702APPGGMR708 are replaced with the conserved 702NKSCAIS708 sequence
oxidosqualene cyclase 7 mutant N478H/V482I
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Oxidosqualene-lanosterol cyclase
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oxidosqualene-lanosterol cyclase mutant H234Y
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cf. EC 5.4.99.7
oxidosqualene:lanosterol cyclase
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cf. EC 5.4.99.7
tetracyclic parkeol synthase
2,3-Oxidosqualene cyclase
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2,3-Oxidosqualene cyclase
Oryza sativa Japonica Group Zhonghua 11
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ERG7
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OSC
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OSC
Oryza sativa Japonica Group Zhonghua 11
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OsOP
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OsOP
Oryza sativa Japonica Group Zhonghua 11
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OsOSC7
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OsOSC7
Oryza sativa Japonica Group Zhonghua 11
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tetracyclic parkeol synthase
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tetracyclic parkeol synthase
Oryza sativa Japonica Group Zhonghua 11
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(3S)-2,3-epoxy-2,3-dihydrosqualene = parkeol
(3S)-2,3-epoxy-2,3-dihydrosqualene = parkeol
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(3S)-2,3-epoxy-2,3-dihydrosqualene = parkeol
reaction from bicyclic C-8 cation (chair-boat form) via protosteryl cation (chair-boat-chair form) to parkeol, proposed reaction scheme of cyclization, overview
(3S)-2,3-epoxy-2,3-dihydrosqualene = parkeol
reaction from bicyclic C-8 cation (chair-boat form) via protosteryl cation (chair-boat-chair form) to parkeol, proposed reaction scheme of cyclization, overview
Oryza sativa Japonica Group Zhonghua 11
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(3S)-2,3-epoxy-2,3-dihydrosqualene mutase (cyclizing, parkeol-forming)
The enzyme from rice (Oryza sativa) produces parkeol as a single product [1].
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(3S)-2,3-epoxy-2,3-dihydrosqualene
orysatinol
(3S)-2,3-epoxy-2,3-dihydrosqualene
parkeol
(3S)-2,3-oxidosqualene
achilleol A + protosta-12,24-dien-3beta-ol + lanosterol + parkeol
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oxidosqualene-lanosterol cyclase mutant H234Y produces a product ratio of 14:26:51:9
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(3S)-2,3-oxidosqualene
cycloartenol + lanosterol + parkeol
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the cycloartenol synthase 1 mutant I481V makes a relative product ratio of 52:26:22
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(3S)-2,3-oxidosqualene
lanosterol + parkeol
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1:1 product ratio
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(3S)-2,3-oxidosqualene
parkeol
(S)-2,3-oxidosqualene
parkeol + cycloartenol + lanosterol
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parkeol is the main product of mutant N478H/V482I
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(S)-2,3-oxidosqualene
parkeol + lanosterol + lanost-24-ene-3beta,9alpha-diol
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lanosterol-synthase mutant T384Y produces 11% parkeol, 79% lanosterol and 10% lanost-24-ene-3beta,9alpha-diol from (S)-2,3-oxidosqualene, lanosterol-synthase mutant T384Y/V4545L produces 60% parkeol, 20% lanosterol and 20% lanost-24-ene-3beta,9alpha-diol from (S)-2,3-oxidosqualene, lanosterol-synthase mutant T384Y/V454I produces 64% parkeol, 13% lanosterol and 23% lanost-24-ene-3beta,9alpha-diol from (S)-2,3-oxidosqualene
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oxidosqualene
lanosterol + parkeol
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mutant H477N produces 88% lanosterol and 12% parkeol, mutant H477Q produces 73% parkeol, 22% lanosterol, and 5% DELTA7-lanosterol
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additional information
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(3S)-2,3-epoxy-2,3-dihydrosqualene
orysatinol
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(3S)-2,3-epoxy-2,3-dihydrosqualene
orysatinol
produced by the double mutants F124L/I732A and F365L/I732A
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(3S)-2,3-epoxy-2,3-dihydrosqualene
orysatinol
Oryza sativa Japonica Group Zhonghua 11
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
orysatinol
Oryza sativa Japonica Group Zhonghua 11
produced by the double mutants F124L/I732A and F365L/I732A
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
parkeol
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(3S)-2,3-epoxy-2,3-dihydrosqualene
parkeol
Oryza sativa Japonica Group Zhonghua 11
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?
(3S)-2,3-oxidosqualene
parkeol
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(3S)-2,3-oxidosqualene
parkeol
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single product
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additional information
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identification of compounds by GC-MS analysis
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additional information
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Oryza sativa Japonica Group Zhonghua 11
identification of compounds by GC-MS analysis
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(3S)-2,3-epoxy-2,3-dihydrosqualene
orysatinol
(3S)-2,3-epoxy-2,3-dihydrosqualene
parkeol
(3S)-2,3-epoxy-2,3-dihydrosqualene
orysatinol
H2KWF1
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
orysatinol
Oryza sativa Japonica Group Zhonghua 11
H2KWF1
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
parkeol
H2KWF1
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?
(3S)-2,3-epoxy-2,3-dihydrosqualene
parkeol
Oryza sativa Japonica Group Zhonghua 11
H2KWF1
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brenda
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brenda
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brenda
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brenda
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UniProt
brenda
Oryza sativa Japonica Group Zhonghua 11
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UniProt
brenda
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brenda
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evolution
molecular evolutionary analysis. Phylogenetic, network and functional analyses of OsOSC7 variants in Oryza sativa subsp. japonica and in Oryza wild-type species, overview
evolution
Oryza sativa Japonica Group Zhonghua 11
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molecular evolutionary analysis. Phylogenetic, network and functional analyses of OsOSC7 variants in Oryza sativa subsp. japonica and in Oryza wild-type species, overview
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physiological function
the OSC from Oryza sativa (OsOP) synthesizes the tetracyclic parkeol as its main product. The OsOP gene is distributed in japonica
physiological function
Oryza sativa Japonica Group Zhonghua 11
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the OSC from Oryza sativa (OsOP) synthesizes the tetracyclic parkeol as its main product. The OsOP gene is distributed in japonica
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additional information
identification of three key amino acid residues amongst 46 polymorphic sites that determine functional conversion between tetracyclic parkeol synthase (OsPS) and pentacyclic orysatinol synthase (OsOS), specifically, the chair-semi(chair)-chair and chair-boat-chair interconversions. Mechanism for the function conversion between OsPS and OsOS. The different orientation of a fourth amino acid residue Y257 is important for functional conversion. Three-dimensional modeling of the enzyme proteins generated by using Homo sapiens LAS structure (PDB ID 1W6K) as a template. Ligand docking
additional information
Oryza sativa Japonica Group Zhonghua 11
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identification of three key amino acid residues amongst 46 polymorphic sites that determine functional conversion between tetracyclic parkeol synthase (OsPS) and pentacyclic orysatinol synthase (OsOS), specifically, the chair-semi(chair)-chair and chair-boat-chair interconversions. Mechanism for the function conversion between OsPS and OsOS. The different orientation of a fourth amino acid residue Y257 is important for functional conversion. Three-dimensional modeling of the enzyme proteins generated by using Homo sapiens LAS structure (PDB ID 1W6K) as a template. Ligand docking
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PAKSY_ORYSJ
759
0
86127
Swiss-Prot
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H477N
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the mutant produces 88% lanosterol and 12% parkeol from oxidosqualene
H477Q
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the mutant produces 73% parkeol, 22% lanosterol, and 5% DELTA7-lanosterol from oxidosqualene
F124L/F365L/I732A
site-directed mutagenesis, the mutant shows reduced parkeol synthesis activity compared to the wild-type and synthesis of other triterpene products
Y257A
site-directed mutagenesis, the mutant shows highly reduced parkeol synthesis activity compared to the wild-type
F124L/F365L/I732A
Oryza sativa Japonica Group Zhonghua 11
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site-directed mutagenesis, the mutant shows reduced parkeol synthesis activity compared to the wild-type and synthesis of other triterpene products
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Y257A
Oryza sativa Japonica Group Zhonghua 11
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site-directed mutagenesis, the mutant shows highly reduced parkeol synthesis activity compared to the wild-type
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Q450H
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nonviable single mutant produces minor amount achilleol A as the sole product
Q450H/V454I
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mutant produces lanosterol, (13alphaH)-isomalabarica-14(26),17E,21-trien-3 beta-ol, protosta-16,24-dien-3beta-ol in a ratio of 75:16:9
T384Y
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mutant produces lanosterol, parkeol, 9beta-lanosta-7,24-dien-3 beta-ol, protosta-13(17),24-dien-3beta-ol and protosta-16,24-dien-3beta-ol in the ratio of 63:31.5:3.5:1:1 without compounds achilleol A and (13alphaH)-isomalabarica-14(26),17E,21-trien-3 beta-ol
T384Y/Q450H
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mutant produces lanosterol, parkeol, 9 beta -lanosta-7,24-dien-3 beta-ol in a ratio of 1:98:1
T384Y/Q450H/V454I
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mutant generates parkeol as the sole product, Vmax/Km 18fold decreased for 3S-2,3-oxidosqualene compared to wild-type
T384Y/V454I
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mutant produces lanosterol, parkeol, 9 beta -lanosta-7,24-dien-3 beta-ol in a ratio of 10:84:6
V454I
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mutant produces poor amounts of lanosterol and (13alphaH)-isomalabarica-14(26),17E,21-trien-3 beta-ol (ratio 90:10)
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expressed in Saccharomyces cerevisiae GIL77 cells; expressed in Saccharomyces cerevisiae strain GIL77
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gene OsOP, from leaf sheath material, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, quantitative RT-PCR expression analysis, recombinant expression in Pichia pastoris strain X33 under the control of the methanol-inducible promoter AOX1
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Segura, M.J.; Lodeiro, S.; Meyer, M.M.; Patel, A.J.; Matsuda, S.P.
Directed evolution experiments reveal mutations at cycloartenol synthase residue His477 that dramatically alter catalysis
Org. Lett.
4
4459-4462
2002
Arabidopsis thaliana
brenda
Sawai, S.; Akashi, T.; Sakurai, N.; Suzuki, H.; Shibata, D.; Ayabe, S.; Aoki, T.
Plant lanosterol synthase: divergence of the sterol and triterpene biosynthetic pathways in eukaryotes
Plant Cell Physiol.
47
673-677
2006
Lotus japonicus
brenda
Khenkin, A.; Neumann, R.
Oxidosqualene Cyclase Residues that Promote Formation of Cycloartenol, Lanosterol, and Parkeol We are grateful to Bridget M. Joubert for advice regarding mutagenesis. We thank Elizabeth A. Hart for an authentic parkeol standard, and for chromatographic and spectroscopic information. This research was funded by the National Institutes of Health (grant no. AI 41598) and the Robert A. Welch Foundation (grant no. C-1323). M.M.M. was an American Society of Pharmacognosy Undergraduate Fellow. M.J.R.S. was a Robert A. Welch Fellow and was supported by an NIH Biotechnology Training Grant (grant no. T32 GM08362).
Angew. Chem.
39
4090-4092
2000
Saccharomyces cerevisiae
brenda
Kimura, M.; Kushiro, T.; Shibuya, M.; Ebizuka, Y.; Abe, I.
Protostadienol synthase from Aspergillus fumigatus: functional conversion into lanosterol synthase
Biochem. Biophys. Res. Commun.
391
899-902
2010
Aspergillus fumigatus
brenda
Wu, T.; Liu, Y.; Chang, C.
Histidine residue at position 234 of oxidosqualene-lanosterol cyclase from Saccharomyces cerevisiae simultaneously influences cyclization, rearrangement, and deprotonation reactions
ChemBioChem
6
1177-1181
2005
Saccharomyces cerevisiae
brenda
Hart, E.; Hua, L.; Darr, L.; Wilson, W.; Pang, J.; Matsuda, S.
Directed evolution to investigate steric control of enzymatic oxidosqualene cyclization. An isoleucine-to-valine mutation in cycloartenol synthase allows lanosterol and parkeol biosynthesis
J. Am. Chem. Soc.
121
9887-9888
1999
Saccharomyces cerevisiae
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brenda
Ito, R.; Mori, K.; Hashimoto, I.; Nakano, C.; Sato, T.; Hoshino, T.
Triterpene cyclases from Oryza sativa L.: cycloartenol, parkeol and achilleol B synthases
Org. Lett.
13
2678-2681
2011
Oryza sativa
brenda
Liu, Y.T.; Hu, T.C.; Chang, C.H.; Shie, W.S.; Wu, T.K.
Protein engineering of Saccharomyces cerevisiae oxidosqualene-lanosterol cyclase into parkeol synthase
Org. Lett.
14
5222-5225
2012
Saccharomyces cerevisiae
brenda
Xue, Z.; Tan, Z.; Huang, A.; Zhou, Y.; Sun, J.; Wang, X.; Thimmappa, R.B.; Stephenson, M.J.; Osbourn, A.; Qi, X.
Identification of key amino acid residues determining product specificity of 2,3-oxidosqualene cyclase in Oryza species
New Phytol.
218
1076-1088
2018
Oryza sativa Japonica Group (H2KWF1), Oryza sativa Japonica Group Zhonghua 11 (H2KWF1)
brenda
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5.4.99.47 parkeol synthase
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